Infusible condensation product of metacresol and formaldehyde.



UNITED STATES PATENT OFFICE LEO H. BAEKELAND, OF YONKERS, NEW YORK, ASSIGNOR TO GENERAL BAKELITE COMPANY, OF NEW YORK, N. 'Y., A CORPORATION OF NEW YORK.

INFUSJiBLE CONDENSATION PRODUCT OF METACRESOL AND FORMALDEHYDE'.

1,088,167 7 No Drawing.

To all whom it may concern:

Be it known that I, Lno H. BAEKELAND, a citizen of the United States, residing at Yonkers, in the county of \Vestchester and State of New York, have invented certain new and useful Improvements in Infusible Condensation Products of Metacresol and Formaldehyde, of which the following is a specification.

It is known that phenol jor oxybenzol (C l-LOH) or its homologues may, under certain special conditions, react upon formaldehyde, (or the polymersof formaldehyde, or products engendering formaldehyde.) with chemical elimination of water, or so-called chemical condensation, to yield insoluble infusible condensation products. The utilization of this reaction for industrial purposes forms the subject-matter of my U. S. Patents Nos. 942,699; 942,700; 942.852; 942,808; 942,809; 939,966; 941,605 and 949,671.

In studying the relative behavior of the homologues of phenols as encountered in phenol mixtures extracted from coal tar, I find that there is a considerable difference in the action of oxybenzol, orthocresol, paracresol and metacresol. With metacresol, the action on formaldehyde is very rapid and energetic, requires relatively small amounts of condensing agents, and gives products of maximum hardness and chemical and physical resistance: oxybenzol acts more slowly and less satisfactorily, while ortho and para" cresol are considerably slower in reacting, require more formaldehyde, stronger condensing agents, or more condensing agent, do not furnish the very hardest bodies, and are more inclined to produce fusible soluble condensation products, which are not desired in processes which aim at the production of hard, strong, resisting, infusible and insoluble products, instead of so-called soluble, fusible shellac substitutes. I thus find that if instead of using for this .purpose ordinary commercial mixtures of phenolic bodies as obtained from coal tar, which contain besides metacresol, variable quantities of oxybenzol (C ILOH) orthocresol, paracresol, xylenols, hydrocarbons and other impurities, I submit this mixture to any process which tends to increase its content of metacresol, and to eliminate substances other than metacresol or oxybenzol (C H OH), I obtain much better results.

Specification of Letters Patent.

Application filed March 14, 1910. Serial No. 549,100.

Patented Mar. 3,1914.

The results are still better if, for this purpose, I employ reasonably pure metacresol, or a mixture of metaoresol one 011 cn ra metacresol and paracresol where the latter is in relatively small proportions, and

which can easily be separated by fractional distillation from commercial mixtures.

In my process, I can use instead of formaldehyde, any of the equivalents of for maldehyde, as for instance its polymers or such substances as are capable of engendering formaldehyde.

The process can be carried out in one or several stages as described in my prior patents and other publications (see Baekeland, Jam-mil Ind. Eng. Ghana, March number, 1909, page 149; August number, 1909, age 545). The condensing process 'or synt esis may be carried out inside of porous bodies,

or suitable fillers may be incorporated with the reacting materials at any stage of the process as described in said prior patent and publications. The process may be facilitated by acid or basic condensing agents and the use of heat or heat and pressure.

In order to increase the amount of metacresol in a commercial mixture of phenols as obtained from the distillation of coal tar, I

can submit same to fractional distillation wherebyoxybenzol and orthocresol will distil first and from this mixture the orthocresol can be separated by fractional freezing, oxybenzol crystallizing first. The latter can then .be added again to the higher boiling fractions which contain mainly metacresol with a smaller amount of paracresol, so that after a proper mixture is made it is found that the percentage of orthocresol has been considerably decreased in the new mixture and the percentage of metacresol has been considerably increased together with that of oxybenzol. Or the whole lighter fraction containing oxybenzol and orthocresol can be. rejected and the higher boiling portion containing mostly .metacrcsol with smaller amounts of paracresol used for reacting upon formaldehyde.

Instead of increasing the percentage of sults may be'accomplished may be used.

1- those of German Patent 100418 to For example I may use the method based upon the difiering solubility of the barium "salts (German Patent 53307 to Riehm); that based upon treatment with chloracetic aci'd (German Patent 79514 to Ledereig or based on special treatment of different salts;

German Patent 112545 to Raschig, separation of the sulfonic derivatives; German Patent 114975 to Raschig, treatment of the sulfonic acids by superheated steam; German Pat'- ents 137584 and 141,421 to Rutgers, separa-\ tion by means of oxalic acid; German Patent 148703 to Ladenburg, treatment with sodium bisulfate containing pyrosulfate; German Patent 152652 to Ladenburg, utilization of lesser solubility of metacresolate of calcium; German Patents 156,761 and 157,616 to Gentsch, useof potash, etc.

I claim:

1. An insoluble and infusible body, containing as an essential constituent a condensation product of formaldehyde and metacresol, and containing corresponding condensation products of paraand orth-cresol only in minor proportions.

2. An insoluble and infusible body, containing as an essentialconstituent a condensatlon productv of formaldehyde and metacresol compounded 'witli'a filling material, and containing corresponding condensation products of para-- and brtho-cresol only in minor proportions.

3. An insoluble and infusible body, 'containing as essential constituents the condensation products of formaldehyde and metacresol, and of-formaldehyde and oxybenzol,

and containing corresponding condensation products of paraand o'rtho-cresol only in minor proportions.

LEO H. BAEKELAND.

' Witnesses H. S. TARBnLL,

MARY L. SHORT. 

